Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 41, Pages 13859-13864Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201301980
Keywords
dynamic kinetic resolution; homoallylic alcohols; lactones; racemization; ruthenium catalysis
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Funding
- Swedish Research Council [621-2010-4737]
- Berzelii Center EXSELENT
- Knut and Alice Wallenberg Foundation
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Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipaseB and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transformed into homoallylic acrylates after hydrolysis of the ester function and subsequent DMAP-catalyzed esterification with acryloyl chloride. After ring-closing metathesis 5,6-dihydropyran-2-ones were obtained in good yields. Selective hydrogenation of the carboncarbon double bond afforded the corresponding -lactones without loss of chiral information.
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